(+)-Lentiginosine, a potent and selective inhibitor of amyloglucosidase: Synthetic efforts and disputes on its absolute configuration

Abstract

(+)-Lentiginosine is a powerful and selective inhibitor of amyloglucosidases and has become a reference compound in the field among derivatives related to imino sugars. The present review focuses on the several total syntheses of this alkaloid, which rely on either a chiral pool or on enantioselective approaches that have appeared since its isolation in 1990. A summary of biological assays and molecular dynamic studies which allowed the assignment of the correct absolute configuration of natural (+)-lentiginosine is reported. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.